Abstract: In his work Ulysses, James Joyce uses the characters of Leopold Bloom and Stephen Dedalus to express his belief about the deconstruction of binaries- both socially and biologically created. Stephen’s preoccupation with ineluctable entelechy prompts him to reject his biological father, Simon, in order to remove this outside influence over his future. In order to completely sever his tie with his father, he must first reject his mother, who represents the link between Simon and Stephen. In doing so, Stephen adopts a new significant mother figure in Leopold Bloom, who becomes a virginal woman who can, and does, bear children in Circe. Bloom’s ability to bypass the gender binary and become a woman serves as a bolster, rather than a hindrance, to his masculinity, because he cannot cuckold himself in the way that Molly has cuckolded him. Moreover, as the child of a virgin mother, Stephen becomes a definitive Messiah figure within the work. Stephen’s position in the work as both an active Messiah and an atheist allows him to avoid the choice of being either religious or non-religious, while Bloom’s position as both a highly sexual character who sexualizes nearly every woman he comes across in town and also a virgin mother removes the choice of being purely abstinent or purely sexual. Stephen’s discourse on Shakespeare introduces an Aristotelian school of thought that mediates the nature of choice, helping to illustrate Joyce’s opinions. Joyce shows his audience that he has two ways of thinking about binaries: Stephen characterizes a ‘neither/nor’ attitude toward binaries decision, while Bloom embodies a ‘both/and’ perspective.